Atropisomeric carbohydrate imidazolidines: A novel class of nonbiaryl atropisomers

Tetrahedron Asymmetry

Volumn 10, Issue 21, 1999, Pages 4071-4074

  Avalos, Martín ^a   Babiano, Reyes ^a   Cintas, Pedro ^a   Higes, Francisco J ^a   Jiménez, José L ^a   Palacios, Juan C ^a   Silvero, Guadalupe ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ISOMERISM; OPTICAL ROTATION; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033406157     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00428-0     Document Type: Article

References (22)

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14. (a) Gimzewski, J. K.; Joachim, C.; Schlittler, R. R.; Langlais, V.; Tang, H.; Johannsen, I. Science 1998, 281, 531-533;
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16. Ikeura, Y.; Ishichi, Y.; Tanaka, T.; Fujishima, A.; Murabayashi, M.; Kawada, M.; Ishimaru, T.; Kamo, I.; Doi, T.; Natsugari, H. J. Med. Chem. 1998, 41, 4232-4-239. These carboxamides exist in the form of two separable rotamers, trans and cis with respect to the amide bond. The potency of the trans rotamer is 7-20-fold higher than that of the cis rotamer. Moreover, the trans isomer can be separated into two stable axially chiral atropisomers, and the (αR)-configuration is required for high-affinity receptor binding.
17. (a) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Valencia, C. Tetrahedron 1993, 49, 2655-2675;
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21. For the configurational notation of axially chiral molecules, see: Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994, p. 1120.
22. 2. The structure was solved by direct methods and refined by full-matrix least-squares with SHELXTL-IRIS. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre: CCDC-104131.